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Brasiliquinone C

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Category Antibiotics
Catalog number BBF-00176
CAS 183201-06-1
Molecular Weight 350.36
Molecular Formula C21H18O5

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Fermentation Lab

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Brasiliquinone C is a benzo-onionquinone antibiotic produced by Nocardia brasiliensis, which has anti-gram-positive bacteria and tumor activity.

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Synonyms (3S)-3-ethyl-6-hydroxy-8-methoxy-3,4-dihydrotetraphene-1,7,12(2H)-trione
IUPAC Name (3S)-3-ethyl-6-hydroxy-8-methoxy-3,4-dihydro-2H-benzo[a]anthracene-1,7,12-trione
Canonical SMILES CCC1CC2=CC(=C3C(=C2C(=O)C1)C(=O)C4=C(C3=O)C(=CC=C4)OC)O
InChI InChI=1S/C21H18O5/c1-3-10-7-11-9-14(23)18-19(16(11)13(22)8-10)20(24)12-5-4-6-15(26-2)17(12)21(18)25/h4-6,9-10,23H,3,7-8H2,1-2H3/t10-/m0/s1
InChI Key JCMDNBJXOUWFMR-JTQLQIEISA-N
Appearance Yellow Powder
Antibiotic Activity Spectrum Gram-positive bacteria; neoplastics (Tumor)
Melting Point 215-217°C
Solubility Soluble in Methanol, chloroform, ethyl acetate, methyl ether
1. Brasiliquinones A, B and C, new benz[alpha]anthraquinone antibiotics from Nocardia brasiliensis. I. Producing strain, isolation and biological activities of the antibiotics
A Nemoto, Y Tanaka, Y Karasaki, H Komaki, K Yazawa, Y Mikami, T Tojo, K Kadowaki, M Tsuda, J Kobayashi J Antibiot (Tokyo). 1997 Jan;50(1):18-21. doi: 10.7164/antibiotics.50.18.
New benz[alpha]anthraquinone antibiotics (brasiliquinones A, B and C) with an ethyl group at C-3 were isolated. The producer was identified as Nocardia brasiliensis. The antibiotics were active against Gram-positive bacteria including Mycobacterium sp., but not active against Gram-negative bacteria or fungi. They were also active against multiple drug-resistant P388/ADR tumor cells.
2. Asymmetric Total Synthesis of Brasiliquinones B and C via Oxidative Cyclization of a Hydroquinone-Silyl Enol Ether Hybrid
Hiroki Miyake, Ryo Nakajima, Takuya Kumamoto J Org Chem. 2022 Sep 16;87(18):12491-12497. doi: 10.1021/acs.joc.2c01653. Epub 2022 Aug 30.
The asymmetric total synthesis of angucycline antibiotics (S)-brasiliquinones B and C was accomplished. The benz[a]anthraquinone core was constructed via oxidative cyclization of a hydroquinone-silyl enol ether hybrid. The resultant pentacyclic acetal was converted to the silyl enol ether, which was treated with Pd(II)/O2 to afford brasiliquinone C, after multistep conversion including dehydrogenation, desilylation and deacetalization, and hydroquinone oxidation. The (S)-configuration of natural brasiliquinones was confirmed based on the stereochemical correlation with the synthetic products.

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